Morency, Louis2013-11-082013-11-0820062006Source: Dissertation Abstracts International, Volume: 67-10, Section: B, page: 5759.http://hdl.handle.net/10393/29366http://dx.doi.org/10.20381/ruor-19714This thesis presents the work done toward the total synthesis of vinigrol. The studies described here are divided into three main approaches. First, the oxy-Cope/Claisen/ene and the oxy-Cope/ene reactions have been developed to provide cis-decalin systems. These methodologies have been applied for the synthesis of the core of vinigrol. Second, a synthetic route that includes the exploitation of the hydroxy-directed Diels-Alder reaction to construct the vinigrol cis-decalin was developed. Two different strategies were developed to close the remaining eight-membered ring: a ring closing metathesis and a Claisen rearrangement. Finally, the sequential hydroxy-directed Diels-Alder/Claisen reaction was adapted for the synthesis of the six- and eight-membered rings of vinigrol.403 p.enChemistry, Organic.Thesis